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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2021-09-14 15:40:08 UTC
HMDB IDHMDB0002197
Secondary Accession Numbers
  • HMDB02197
Metabolite Identification
Common Name7a,12a-Dihydroxy-cholestene-3-one
Description7a,12a-Dihydroxy-cholestene-3-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 7a,12a-Dihydroxy-cholestene-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752235
Synonyms
ValueSource
7-a,12-a-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-a-Dihydroxycholest-4-en-3-oneHMDB
7-a,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7-alpha,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-alpha,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7alpha,12alpha-Dihydroxy-cholestene-3-oneHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
Traditional Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyVJGNBLOGSXHTLR-JFXJTJEYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP10(4.69) g/LALOGPS
logP10(5.18) g/LChemAxon
logS10(-5.2) g/LALOGPS
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.94 m³·mol⁻¹ChemAxon
Polarizability50.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.94831661259
DarkChem[M-H]-199.72431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7a,12a-Dihydroxy-cholestene-3-one,1TMS,#1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O3441.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,1TMS,#2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C3401.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,1TMS,#3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O3308.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TMS,#1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C3353.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TMS,#2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O3289.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TMS,#3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C3232.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,#1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O3660.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,#2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3610.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,1TBDMS,#3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O3552.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,#1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3778.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,#2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O3745.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-cholestene-3-one,2TBDMS,#3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)C=CC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C3678.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0957100000-f9ca360b20be30aee5cd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6421590000-060d19b9863c108036ea2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Positive-QTOFsplash10-00kb-0009200000-ca011752a678df923d912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Positive-QTOFsplash10-007k-2109000000-fe2eac67f433d8e5ffd62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Positive-QTOFsplash10-0avi-7209000000-dd9edd2da2f8a7cfa3b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Negative-QTOFsplash10-014i-0004900000-9a4838827d7cc0003b0c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Negative-QTOFsplash10-014j-0009800000-d99dd5a2761313bbd19c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Negative-QTOFsplash10-0012-1109000000-12f6e81d23b56a07105c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Positive-QTOFsplash10-014i-0005900000-6e10002b2e4a4ff637042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Positive-QTOFsplash10-052r-6369100000-1f4ae070beee131b40ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Positive-QTOFsplash10-0a6u-9530000000-59dfe5c229199b50616d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 10V, Negative-QTOFsplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 20V, Negative-QTOFsplash10-014i-0001900000-949821f2e2f9dbbe86322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-cholestene-3-one 40V, Negative-QTOFsplash10-0udr-0079200000-cad453714d3d5275e24b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022899
KNApSAcK IDNot Available
Chemspider ID13628315
KEGG Compound IDC05457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6539
PubChem Compound21252277
PDB IDNot Available
ChEBI ID28477
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bjorkhem I, Oftebro H, Skrede S, Pedersen JI: Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. J Lipid Res. 1981 Feb;22(2):191-200. [PubMed:7017048 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 7a,12a-Dihydroxy-cholestene-3-one + NADPH + Hydrogen Iondetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A2
Uniprot ID:
P31213
Molecular weight:
28407.035
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
General function:
Involved in monooxygenase activity
Specific function:
Involved in bile acid synthesis and is responsible for the conversion of 7 alpha-hydroxy-4-cholesten-3-one into 7 alpha, 12 alpha-dihydroxy-4-cholesten-3-one. Responsible for the balance between formation of cholic acid and chenodeoxycholic acid. Has a rather broad substrate specificity including a number of 7-alpha-hydroxylated C27 steroids.
Gene Name:
CYP8B1
Uniprot ID:
Q9UNU6
Molecular weight:
58068.01
Reactions
7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails
7a-Hydroxy-cholestene-3-one + Hydrogen Ion + Oxygen + NADPH → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails